1-Amino-2-propanol → N1-(2-hydroxypropyl)-N2-(3-(trifluoromethyl)phenyl)oxalamide

HRID 1640693Notes

Reaction equation

HRID 1640693 reaction equation
[O:1]=[C:2]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=1)[C:3]([O:5]CC)=O.[NH2:19][CH2:20][CH:21]([OH:23])[CH3:22]>C(O)C>[OH:23][CH:21]([CH3:22])[CH2:20][NH:19][C:3](=[O:5])[C:2]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:16])([F:17])[F:18])[CH:10]=1)=[O:1]

Participants

4

Reactant 2

HCID 41-Amino-2-propanolHCID 1805242ethyl 2-oxo-2-[3-(trifluoromethyl)anilino]acetate

Product 1

HCID 2917089N1-(2-hydroxypropyl)-N2-(3-(trifluoromethyl)phenyl)oxalamideYield 99%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl oxo{[3-(trifluoromethyl)-phenyl]amino}acetate (8.04 g, 30.7 mmol) was dissolved in ethanol (50 ml, 99.5%). To the stirred solution was added 1-amino-2-propanol (racemic, 2.32 g, 31 mmol) in one portion, and the mixture was heated to reflux for 90 minutes. The mixture was allowed to cool and was evaporated to dryness, giving 8.80 g (99%) of N-(2-hydroxypropyl)-N′-[3-(trifluoromethyl)-phenyl]ethanediamide as a white solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 90 minutes
  3. temperatureto cool
  4. customwas evaporated to dryness

Sources & evidence

ORD record
ord-1b20ee5950e34c4284306e7845bb5a43
Source dataset
uspto-grants-2012_02
Patent number
US08114881B2

Reaction notes

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